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If I was to request an image over HTTPS and record the packets over WireShark and then inspect a peer's Wireshark and look for the same packets, would I be able to see if they requested the same file, whether it's at the same host or a different one?

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    Question headline appears misleading. Commented Jan 13, 2016 at 5:14

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No.

The session key under which the data is actually encrypted is derived randomly.

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  • is this for both HTTPS and SSH? Commented Jan 13, 2016 at 12:49
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    Yes, it's true for all competently-written crypto.
    – tylerl
    Commented Jan 13, 2016 at 18:01

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